Hydrochloric Acid → HCID 13006793, compound

HRID 1250424Notes

Reaction equation

HRID 1250424 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=2)(=[O:18])=[O:17])(=[O:14])=[O:13])=[CH:8][CH:7]=1)(=[O:4])=[O:3].C1(C)C=CC(S([N:39]=[N+:40]=[N-])(=O)=O)=CC=1.C1CCN2C(=NCCC2)CC1.Cl>ClCCl>[CH3:29][S:26]([O:25][C:22]1[CH:23]=[CH:24][C:19]([S:16]([C:15]([S:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:11][CH:10]=2)(=[O:14])=[O:13])=[N+:39]=[N-:40])(=[O:17])=[O:18])=[CH:20][CH:21]=1)(=[O:28])=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13661p-Toluenesulfonyl azideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13006792HCID 13006792, compound

Product 1

HCID 13006793HCID 13006793, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The bis(4-methylsulfonyloxyphenylsulfonyl)methane in Synthesis Example 3, 9.7 g (0.02 mol), was dispersed in 97 g of dichloromethane. To the dispersion was added 4.6 g (0.03 mol) of p-toluenesulfonylazide which had been separately prepared. With stirring at room temperature, 5.9 g (0.03 mol) of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) was added to the dispersion, and after 5 minutes, 150 g of a 0.2N aqueous hydrochloric acid was added to stop reaction. The organic layer was separated and washed with 100 g of water. The organic layer was concentrated and 14 g of the residue was purified by silica gel column chromatography using dichloromethane as an elute. The thus obtained oily product was combined with 40 g of hexane for crystallization, followed by filtration and vacuum drying. There was obtained 3.0 g (yield 29%) of fine yellow crystals.

Workup

  1. customhad been separately prepared
  2. customreaction
  3. customThe organic layer was separated
  4. washwashed with 100 g of water
  5. concentrationThe organic layer was concentrated
  6. custom14 g of the residue was purified by silica gel column chromatography
  7. customThe thus obtained oily product was combined with 40 g of hexane for crystallization
  8. filtrationfollowed by filtration and vacuum
  9. customdrying

Sources & evidence

ORD record
ord-1a14de14496a468fa179d8c4d543b771
Source dataset
uspto-grants-2002_01
Patent number
US06338931B1

Reaction notes

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